Ryan Reynolds Dating History: How Many Actresses Did He Dated Before Marrying Blake Lively?

By Rahul Rajput On Feb 8, 2023

Ryan Reynolds Dating History: When one of our favorite couples is having such a great time together now, it’s difficult to reflect on their former relationships. Ryan Reynolds, star of “Deadpool,” and Blake Lively, one of the most popular actresses in Hollywood, are always spreading good vibes and love. The couple always seems to be having a good time together, and their followers really appreciate that.

It’s impossible to imagine Reynolds and Lively’s lives apart from their wedding day because they each have extensive dating histories. Indeed, Reynolds and Lively went on a double date together, bringing along their respective significant others. Before settling down with the ‘Gossip Girl actress, let’s learn who else the ‘Green Lantern’ star is dating.

1. Melissa Joan Hart

It was in the film “Sabrina, the Teenage Witch” that Reynolds and Melissa Joan Hart co-starred. At the time of their passionate makeout session following their interview with Chelsea Handler, Ryan was 17 and Melissa was 19. He won her heart with his charm and the gift of a Beluga watch.

Melissa said that Ryan’s wife Blake Lively knows about their on-set affair and even requested Melissa to “help her find a birthday present for Ryan” in her 2016 memoir, “Melissa Explains It All: Tales From My Abnormally Normal Life.”

2. Traylor Howard

Traylor Howard and Ryan Reynolds starred in the ABC sitcom “Two Guys, a Girl, and a Pizza Place” in 1998, after his romance with Melissa. After eight months of dating, the couple broke up. It has been announced that the 56-year-old actress is married to Jarel Portman, a businessman, and musician.

3. Kristen Johnston

Ryan Reynolds dated Kristen Johnston for five months.

In an interview with ‘Watch What Happens Live presenter Andy Cohen, the actress, who is ten years older than Reynolds, talked about her past relationship with the actor. Johnston called Reynolds a “wonderful guy” and said they went to the premiere of Tom Hanks’ thriller “The Green Mile” together.

4. Rachael Leigh Cook

After starring in blockbuster movies like She’s All That and The Baby-Sitters Club, Rachael Leigh Cook was at the pinnacle of her acting career in 2001. However, Ryan had recently ended his relationship with Kristen Johnston after dating her for a year.

According to Netflix Junkie, Free Guy’s star traveled all the way to London to woo Rachel Leigh Cook, but the two were never spotted together in public after their alleged tryst. During 2001, they dated briefly.

5. Alanis Morissette

In 2002, the Adam Project actor started dating the Hand in my Pocket singer. Clearly, fate brought these two together in the Great White North. According to reports, the couple became engaged in 2004, only to break up nearly three years later. They dated from 2002 to 2007, making up over half of that time.

In fact, 2008’s Flavors of Entanglement was Morissette’s album that most directly addressed the breakup. Ryan was the inspiration for the heartbreaking song Torch.

6. Scarlett Johansson

The Definitely, Maybe star fell deeply in love with Scarlett Johansson, star of Black Widow, after his 2007 split from Alanis. Scarlett had recently ended her engagement to actor Josh Hartnett at the time.

In 2008, Ryan and Scarlett married in secret. Reynolds’s birthplace of Vancouver served as the setting for the intimate wedding ceremony when the couple exchanged vows in front of immediate relatives and friends. No pictures from the couple’s wedding were made public.

The actress from Lost in Translation discussed the exclusive event in a previous interview with the Los Angeles Times. Then she said, “I needed to get away by myself for a while and do something I enjoyed.” Overall, I was pleased with the outcome of that.

7. Bullock

Ryan Reynolds’ co-star in “The Proposal,” Sandra Bullock, began dating him in 2011. The “Miss Congeniality” star has denied relationship rumors involving Ryan Reynolds. She and Ryan have been “great friends” for 10 years, she said in an interview.

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8. Agnes Fischer

Ryan didn’t wait long to get back on the dating scene after he and Scarlett split up. He was rumored to have dated the German fashion model Agnes Fischer during the time. They dated for a short time, maybe a few months max.

9. Charlize Theron

Charlize Theron was prepared to “settle” and “be more serious,” whereas Ryan Reynolds preferred a “casual” approach. Reynolds dated Theron for two months before starting a family with Blake Lively; the two of them had been introduced by mutual friends.

10. Blake Lively

The first time Ryan and his future wife Blake met was on the set of Green Lantern in 2010, but they didn’t start dating until the following year because they were both in committed relationships with other people at the time. Reynolds was married to actress Scarlett Johansson at the time, while Lively was seeing her Gossip Girl co-star Penn Badgley.

Blake and Penn reportedly broke up in October 2010. From 2007 through 2010, they had an on-and-off relationship. Ryan and Scarlett, who had been married for two years, filed for divorce in December of that year, and their divorce was finalized in July 2011.

The greatest way to build a relationship, I think, is to start as friends, as Ryan said during an interview on SiriusXM’s Entertainment Weekly Radio’s Deadpool special in 2016.